1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for

Details 1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for 1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for

1984-11-14

1985-10-29

Albrecht, Dennis L.

Compositions

Durable finishes for textile materials, or processes of...

Oil or water repellent or soil resistant or retardant

252132, 25217411, 252522A, C07C 3522, C07C 3531, C11D 350, C11D 944

Patent

active

045499721

ABSTRACT:
Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

REFERENCES:
patent: 3869524 (1975-03-01), Light et al.
patent: 3914322 (1975-10-01), Chappell
Chemical Abstracts, vol. 70, 1969, p. 303, Abstract No. 11834w, Danishefsky, S., "Total Synthesis of Racemic Patchouli and Epi-Patchouli Alcohol".
Chemical Abstracts, vol. 87, 1977, p. 478, Abstract No. 39023f, Light, K., "Tricyclic Alcohols".
Chemical Abstracts, vol. 89, 1978, p. 553, Abstract No. 129095b, Gompper, R., "Bicyclo[2.2.2]Octa-5,-7-Diene-2-One (Barrelenone)".
Chemical Abstracts, vol. 91, 1979, p. 557, Abstract No. 107702m, Gompper, R., "Bicyclo[2.2.2]Octa-5,-7-Diene-2-Carboxylic Acid and 7-Methylene-Bicyclo[2.2.2]Octa-2,5-Diene".

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